So, it looks like good news bad news to me ... First, the pathwatch thread is executed. However, it is not apparent that the password(s) are being updated. It's only ASSUMED that the hash is updated. There's no way to tell with this debug output that the passwords were in fact updated. Anyway to see the updated password values? I'm using 9.3.11.v20160721. I am using curl for this test.
2016-09-15 20:00:33.207:DBUG:oejs.PropertyUserStore:main: Loading org.eclipse.jetty.security.PropertyUserStore[users.count=0identityService=org.eclipse.jetty.security.DefaultIdentityService@2bbaf4f0] from /security.properties
2016-09-15 20:00:33.212:DBUG:oejs.HashLoginService:main: update: u6 Roles: 1
2016-09-15 20:00:33.212:DBUG:oejs.HashLoginService:main: update: u5 Roles: 1
2016-09-15 20:00:33.212:DBUG:oejs.HashLoginService:main: update: u4 Roles: 1
2016-09-15 20:00:33.212:DBUG:oejs.HashLoginService:main: update: u3 Roles: 1
2016-09-15 20:00:33.212:DBUG:oejs.HashLoginService:main: update: u2 Roles: 1
2016-09-15 20:00:33.212:DBUG:oejs.HashLoginService:main: update: u1 Roles: 1
2016-09-15 20:00:33.213:DBUG:oejs.PropertyUserStore:main: Loaded org.eclipse.jetty.security.PropertyUserStore[users.count=6identityService=org.eclipse.jetty.security.DefaultIdentityService@2bbaf4f0] from /security.properties
2016-09-15 20:00:33.216:INFO:oeju.PathWatcher:main: Using Non-Native Java sun.nio.fs.PollingWatchService
2016-09-15 20:00:33.216:WARN:oeju.PathWatcher:main: Quiet Time is too low for non-native WatchService [sun.nio.fs.PollingWatchService]: 1000 < 5000 ms (defaulting to 5000 ms)
2016-09-15 20:00:33.264:INFO:oejsh.ContextHandler:main: Started o.e.j.s.h.ContextHandler@5606c0b{/security,null,AVAILABLE}
2016-09-15 20:00:33.264:INFO:oejsh.ContextHandler:main: Started o.e.j.s.h.ContextHandler@80ec1f8{/keys,null,AVAILABLE}
2016-09-15 20:00:33.264:INFO:oejsh.ContextHandler:main: Started o.e.j.s.h.ContextHandler@1445d7f{/images,null,AVAILABLE}
2016-09-15 20:00:33.265:INFO:oejs.Server:main: jetty-9.3.z-SNAPSHOT
2016-09-15 20:00:33.285:INFO:oejs.AbstractConnector:main: Started ServerConnector@358c99f5{HTTP/1.1,[http/1.1]}{0.0.0.0:8080} 2016-09-15 20:00:33.305:INFO:oejus.SslContextFactory:main: x509=X509@7920ba90(1,h=[www.vizorfy.com],w=[]) for SslContextFactory@6b419da(file:///keystore,file:///vz-cit/keystore) 2016-09-15 20:00:33.432:INFO:oejs.AbstractConnector:main: Started ServerConnector@36fc695d{SSL,[ssl, http/1.1]}{0.0.0.0:8443} 2016-09-15 20:00:33.433:INFO:oejs.Server:main: Started @847ms
2016-09-15 20:01:23.230:DBUG:oejs.PropertyUserStore:PathWatcher-Thread[/]: Loading org.eclipse.jetty.security.PropertyUserStore[users.count=6identityService=org.eclipse.jetty.security.DefaultIdentityService@2bbaf4f0] from /security.properties
2016-09-15 20:01:23.230:DBUG:oejs.HashLoginService:PathWatcher-Thread[/]: update: u6 Roles: 1
2016-09-15 20:01:23.230:DBUG:oejs.HashLoginService:PathWatcher-Thread[/]: update: u5 Roles: 1
2016-09-15 20:01:23.230:DBUG:oejs.HashLoginService:PathWatcher-Thread[/]: update: u4 Roles: 1
2016-09-15 20:01:23.231:DBUG:oejs.HashLoginService:PathWatcher-Thread[/]: update: u3 Roles: 1
2016-09-15 20:01:23.231:DBUG:oejs.HashLoginService:PathWatcher-Thread[/]: update: u2 Roles: 1
2016-09-15 20:01:23.231:DBUG:oejs.HashLoginService:PathWatcher-Thread[/]: update: u1 Roles: 1
2016-09-15 20:01:23.231:DBUG:oejs.PropertyUserStore:PathWatcher-Thread[/]: Loaded org.eclipse.jetty.security.PropertyUserStore[users.count=6identityService=org.eclipse.jetty.security.DefaultIdentityService@2bbaf4f0] from /security.properties